It is common for front seating assemblies in vehicles to include a headrest assembly for supporting the head of a seated occupant. Generally, these headrest assemblies are installed separately on a vehicle seat in a vehicle manufacturing facility after the vehicle seat has been installed in a vehicle interior. This is generally due to the fact that when assembled, the vehicle seat in combination with the headrest assembly is too large to fit through the front driver's side or passenger's side doors. Further, an assembled seat with headrest is often too large to ship as a unitary structure on a typical trailer storage shelf. Thus, they are typically installed separately which incurs higher costs and a number of undesired installment executions. Further, making electrical and structural connections between the vehicle seat and the headrest assembly is an assembly execution that is better performed when the vehicle seat is not installed in the vehicle. Further still, known headrest assemblies may be limited to vertical adjustment relative to a seatback, such that these headrest assemblies lack adequate adjustment features for different sized occupants and various positions a seated occupant may assume in the vehicle seat.